Abstract
Various kinds of aminocinnamic acid derivatives were hydrogenated with different stereoselectivities. In the presence of cinchonidine or (−)-dihydroapovincaminic acid ethyl ester modifiers, the enantioselective hydrogenations resulted in very low enantiomeric excesses (ee). Moderate diastereomeric excesses (de, 5–68%) were achieved in the diastereoselective hydrogenations. The highest de (68%) was obtained in the hydrogenation of N-acetyldehydrophenylalanyl-( S)-prolinanilide due to a 10-member intermediate stabilized by hydrogen bond.
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